OOC: I am assuming you but Kileprat's name in the initiative instead of Storm's by mistake?

Ya that's my bad.

Order: Stage, Aino, Casey, Syndicate member (SM) 1, 2, 3, 4 ,5, 6, Storm, SM 7, 8, 9, 10, SL (too far to attack) 

Aino is up

Ok @Bushawk - I want to run the plan by you.  With theater of the mind as we are doing, maybe I'm not getting the right picture.  So maybe what I'm going to suggest is obviously not possible, but hopefully with Aino having 20 INT, she'd be able to figure it out in advance and not try it then.

Her plan is to hold on to Thumbtack under her arm and touch Storm on his shoulder.  She then casts Dimension Door to teleport them (leaving Casey behind unfortunately) 500' into the middle of the Syndicate members.  Note that Dimension Door allows you to bring anything you're holding up to carrying capacity plus one more creature up to your size (medium, which I think Storm is).

Her idea is that in the middle of the huge expanse of Syndicate members, only the handful next to them (maybe 10-12) will be able to attack and the others won't be able to get close enough.  Most of the archers should be blocked too if they don't want to shoot their own allies.  In the fog of war, most of the Syndicate folks won't even know where they are because view to them will be blocked off by the mass of Syndicate members.  All our communication is telepathic (Rary's Telepathic Bond) so they can't hear what we're trying to do.  It should be surprising to them.

Round 2:  Aino is going to cast Dimension Door again, another 500' to get to the Syndicate leader who is 1000' away, again bringing Storm with her (and holding onto Thumbtack).  Note that unlike with Misty Step, the caster does not have to see the destination with Dimension Door.

Let me know if, based on the layout and spacing, this looks like it will work to Aino.

It is possible I'll make you roll a perception as a free action before you do it though to see if you pick an occupied spot. Will also do a perception check for rose around you to see if they spot you on the turn you arrive. 

Ok.  I'm hoping the fact that we're all flying in the air currently makes it easier to look ahead and down and pick an unoccupied spot.  I'm also going to have Aino use a Lucky feat roll and or Bardic Inspiration possibly here.

Ok, no Lucky feat or Bardic inspiration needed.

Aino Perception:  26 (18 + 8)

Through her telepathic bond, Aino asks urgently:  Storm, let me do this.  Don't resist the teleportation.  We are headed to the Syndicate leader on the double.  Casey can't come (wish I could bring all three of us) but she is going to go invisible and fly over when she can.

From just above Storm's head on her Broom of Flying, with Thumbtack nestled in one hand and her Rapier, +3 sheathed, Aino casts Dimension Door 500' ahead to a small gap among the Syndicate's men, making a beeline for the leader.  She brings Storm.

Hoping that at least the men we just teleported past are still looking ahead and don't know where we went as Aino and Storm teleport.

No further movement or bonus action but to stay close to Storm at ground level halfway in the middle of the Syndicate's forces, back to back with the paladin.  Hoping that even if archers see Aino and Storm, only a few of them have a clear shot with the two being in the middle of all their allies.

Casey, flying high on her broom, looks at the horde of fighters, and yells out “You syndicate clowns must be real cowards to cheat this bad!”  Taking her Bandore in hand, she strums a chord and disappears.  invisibility Immediately after, she makes a beeline at maximum speed on her broom, climbing to  40’ in the air and flying invisibly towards the syndicate leader, far down the battlefield…

That all happens. Aino and Storm pop out about 60 ft from the second LT. The rank and file near by is surprised. A Sgt and LT2 both clock your arrival. The SGT rolled a 22 on int so he will get an attack this round the LT is too slow to react.

The 5 you left behind are confused on where yall went. But one of them rolled a 21 on perception but only a 13 on int. He herd Casey flying over head but thinks yall are going for the first LT.

He shouts They are going after the LT!

Word starts to spread around the ranks.

Storm is up. Then the SGT then the SM by Casey.

Storm will use the dodge action, and that is it.

OOC: Apologies I somehow missed that Storm was up.

No worries. Long day at work. Will post tomorrow 

The veteran turns to attack. He will shoot with his crossbow at storm nat 20 to hit for 21 damage. (I no joke rolled 2 nat 20s shame it was on such a weak attack)

He will also yell. There they are get em boys.

Next round Aino is up

OOC: Dont forget that Storm is immune to crits, so is the damage still 21?

Yeah I'm thinking the crit damage should turn into regular damage with adamantine armor and not worth a use of Silvery Barbs.

Storm still needs a DC10 CON Save to maintain concentration on Bless.

Aino flies up just a few feet on her Broom of Flying.  Not leaving anyone's threatened range.  With the bottom of one foot still touching Storm's shoulder, she surveys and locates a spot just next to the Syndicate Leader 500' away.

Holding Thumbtack, Aino casts Dimension Door once more, teleporting 500' with Storm to place herself and Storm in melee with the Syndicate Leader.  She does not make any noise, hoping to be at the side so it is not obvious in the fog of war what has happened.

Thumbtack then flies in the face of the Syndicate Leader and back to Aino's shoulder, taking the help action, granting advantage to Storm's first attack.  Aino herself circles around, still on the Broom of Flying next to the Syndicate Leader in melee, but not in the way of any blast Storm does.

Right righr, its 10 damage

Casey’s Turn:  not the most exciting.   Invisible, flying 60’ above the battlefield and trying to stay quiet, she dashes 100’ towards her friends.  She will get there in like 10 rounds at this rate.  .  If they succeed in taking down the leader,  or something else happens, she might do something else.  

Aino make another per perception roll. 

Casey you feel a strange cold sensation come over you as you fly. A dark void opens infrot of you you can't avoid. 

Death sitting on a couch watch a TV with the fight on looks at you.

"Sup girl, you look like you needed a boost"

You come out right above the Syndicate Leader. Confused and disoriented you feel a bit lost. Make a perception check to get your bearings.

Aino Perception:  15 using both a die from the Lucky Feat (1st of 3 Lucky dice) to re-roll plus Casey's Bardic Inspiration.

(First roll before using Lucky was a nat. 1, next was a 5 on the die, + 8 bonus for 13, rolled the d10 Bardic Inspiration and got a 2 for a 15).

With a 15 you see an open space but it's 30 feet away. Between you and the SL is hard his personal guard. 6 total guards plus the SL. There is also 14 rank and file in the area.

They enter combat on the next round.

Storm is up

(Then Thumbtack takes the help action instead on whoever it looks like Storm can get to so he has advantage on the first attack if he makes one).